1,2,3,5-Tetraacetyl-beta-D-ribofuranose → 2-Amino-5,6-dichloro-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)benzimidazole

HRID 2379058

Reaktionsgleichung

Reaktionsgleichung von HRID 2379058
[NH2:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([Cl:11])[C:8]([Cl:12])=[CH:7][C:5]=2[N:6]=1.C(O[C@@H:17]1[O:29][C@H:28]([CH2:30][O:31][C:32](=[O:34])[CH3:33])[C@@H:23]([O:24][C:25](=[O:27])[CH3:26])[C@H:18]1[O:19][C:20](=[O:22])[CH3:21])(=O)C.[Si](S(C(F)(F)F)(=O)=O)(C)(C)C>C(#N)C>[NH2:1][C:2]1[N:3]([C@@H:17]2[O:29][C@H:28]([CH2:30][O:31][C:32](=[O:34])[CH3:33])[C@@H:23]([O:24][C:25](=[O:27])[CH3:26])[C@H:18]2[O:19][C:20](=[O:22])[CH3:21])[C:4]2[CH:10]=[C:9]([Cl:11])[C:8]([Cl:12])=[CH:7][C:5]=2[N:6]=1

Komponenten

5

Edukt 3

HCID 830641,2,3,5-Tetraacetyl-beta-D-ribofuranoseHCID 4660162-Amino-5,6-dichlorobenzimidazoleHCID 13257444Trifluoromethyl(trimethylsilyl) sulfone

Produkt 1

HCID 100498762-Amino-5,6-dichloro-1-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)benzimidazoleAusbeute 15,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

2-Amino-5,6-dichlorobenzimidazole (4) (3 g, 16 mmole) was dissolved in dry acetonitrile (150 ml) and stirred in an insert atmosphere at 60° C. BSA (4.37 ml, 17 mmole) was added and the mixture was stirred for 10 minutes. 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose (5.09 g, 16 mmole) and TMSTf (3.29 ml, 17 mmole) were added to the clear solution and the mixture was allowed to stir at 60° C. for 1 hr. The mixture was concentrated under reduced pressure and separated on a silica column to yield 1.14 g (15%) of 2-amino-5,6-dichloro-1-(2,3,5,tri-O-acetyl-β-d-ribofuranosyl) benzimidazole (43). --C NMR (CDCl3): d 170.04 ppm, 169.56, 169.11, 154.57, 141.64, 132.53, 125.90, 1123.45, 117.72, 109.49, 85.78, 80.99, 70.95, 69.83, 62.91, 20.74, 20.54, 20.20. 1H NMR (CDCl3): d 0.96 ppm (s, 3H), 1.09 (s, 3H), 1.13 (s, 3H), 3.75 (m, 2H), 4.08 (dd, 1H), 5.00 (dd, 1H), 5.13 (t, 1H), 5.42 (s, 2H), 5.61 (d, 1H), 7.27 (s, 1H), 7.42 (s, 1H). MS (FAB): m/e 758, 718, 676, 460, 426, 259, 217, 139.

Aufarbeitung

  1. additionBSA (4.37 ml, 17 mmole) was added
  2. stirringthe mixture was stirred for 10 minutes
  3. stirringto stir at 60° C. for 1 hr
  4. concentrationThe mixture was concentrated under reduced pressure
  5. customseparated on a silica column

Quellen und Nachweise

ORD-Eintrag
ord-920f1d12835f4eb0b3b329e1e67a711c
Quelldatensatz
uspto-grants-1994_11
Patentnummer
US05360795

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